Structural characterization of dimethyl‐ and di‐<i>n</i>‐butyltin(IV) 2,3‐pyridinedicarboxylate in solution and in the solid state

Garcı́a-Zarracino, Reyes; Höpfl, Herbert

doi:10.1002/aoc.773

Cited by 12 publications

(8 citation statements)

References 45 publications

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“…Admittedly this field is quite nascent, but the recent results in this area are quite exciting. Recently, Höpfl and co-workers utilized covalent as well as noncovalent interactions for the assembly of a diorganotin carboxylate-based three-dimensional porous supramolecular network. − We have recently reported supramolecular networks of organostannoxanes containing ferrocenyl and other substituents. − In these assemblies, the supramolecular formation is assisted by a combination of noncovalent interactions including O−H···O, C−H···O, C−H···F, C−F···π, C−H···π, and π-stacking interactions. To understand the influence of secondary interactions on supramolecular structures in organostannoxane compounds, we have decided to adopt a systematic approach.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, Ho ¨pfl and co-workers utilized covalent as well as noncovalent interactions for the assembly of a diorganotin carboxylate-based three-dimensional porous supramolecular network. [36][37][38][39] We have recently reported supramolecular networks of organostannoxanes containing ferrocenyl and other substituents. [40][41][42][43][44] In these assemblies, the supramolecular formation is assisted by a combination of noncovalent interactions including O-H‚‚‚O, C-H‚‚‚O, C-H‚‚‚F, C-F‚‚‚π, C-H‚‚‚π, and π-stacking interactions.…”

Section: Introductionmentioning

confidence: 99%

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Influence of Aromatic Substituents on the Supramolecular Architectures of Monoorganooxotin Drums

Chandrasekhar

Gopal

Nagendran

et al. 2005

Crystal Growth & Design

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The reaction of n-BuSn(O)(OH) with various substituted benzoic acids affords hexameric organostannoxane drums, [n-BuSn(O)OC(O)R] 6 , where R ) 2,6-(CH 3 ) 2 -C 6 H 3 (1), 4-CH 3 -C 6 H 4 (2), 4-NH 2 -C 6 H 4 (3) and 2-NH 2 -C 6 H 4 (4). The central stannoxane motif (Sn 6 O 6 ) is similar in all these compounds and is surrounded by six substituted benzoate groups. All the drums show an extensive supramolecular organization in the solid state. Accordingly, drum 1 forms a one-dimensional supramolecular assembly mediated by noncovalent interactions such as C-H‚‚‚O and π‚‚‚π interactions. Similarly, drums 2-4 form interesting three-dimensional supramolecular assemblies mediated by C-H‚‚‚O, N-H‚‚‚N, C-H‚‚‚π, and π‚‚‚π interactions in the solid state. The role of the peripheral aromatic substituents in determining the final course of the supramolecular assembly is discussed.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Influence of Aromatic Substituents on the Supramolecular Architectures of Monoorganooxotin Drums

Chandrasekhar

Gopal

Nagendran

et al. 2005

Crystal Growth & Design

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“…These experiments yielded crystalline substances suitable for single-crystal X-ray diffraction analysis (SCXRD) with pyridine, benzyl alcohol, and nitrobenzene, viz., [Me 2 Sn(25pdc)(py)] 3 ·3.04C 5 H 5 N·1.86H 2 O ( 1 ), {[Me 2 Sn(25pdc)][Me 2 Sn(25pdc)(H 2 O)]} n ·2 n C 7 H 8 O ( 2 ), and {[ n Bu 2 Sn(25pdc)] 4 } n ·4 n C 6 H 5 NO 2 ( 3 ). Since the molecular and supramolecular structures of diorganotin pyridinedicarboxylates are influenced by the presence of alcohols, ,, n Bu 2 SnO was combined with 25pdcH 2 also in the presence of 1,2-ethanediol (glycol) giving crystals of composition [ n Bu 2 Sn(25pdc)(gly)] n ( 4 ). Upon replacement of 1,2-ethanediol with 1,3-propane- and 1,4-butanediol, only the latter reaction gave, in a solvent mixture with chloroform, single crystals of composition {[ n Bu 2 Sn(25pdc)] 3 } n · n CHCl 3 ( 5 ).…”

Section: Resultsmentioning

confidence: 99%

“…Using a building block formed from Cu(II) and 25pdc in a 1:2 stoichiometric ratio, Chandrasekhar’s group generated an interesting heterobimetallic 2D MCP in combination with trimethyltin fragments . Our own research group reported the formation of supramolecular diorganotin assemblies based on 23pdc and 25pdc, giving (i) trinuclear macrocyclic ring structures of composition [ n Bu 2 Sn(25pdc)(DMSO)] 3 ·3DMSO, [Ph 2 Sn(25pdc)(DMSO)] 3 ·5DMSO, and [( n Bu) 2 Sn(25pdc)(H 2 O)] 3 ·1.5H 2 O·3ROH with R = Et and Pr, , and (ii) 1D and 3D coordination polymers of composition [Me 2 Sn(25pdc)(H 2 O] n · n EtOH, [Me 2 Sn(23pdc)(DMSO)] n · n DMSO, [ n Bu 2 Sn(23pdc)(solv)] n with solv = H 2 O and MeOH, and {[ n Bu 2 Sn(25pdc)] 3 } n ·3 n MeOH· n H 2 O . Somewhat related MCPs were synthesized by Loye’s group upon reaction of Sn(II) ions with 25pdc .…”

Section: Introductionmentioning

confidence: 99%

Pyridinedicarboxylic Acids as Versatile Building Blocks for Coordination-Driven Self-Assembly: Solvent-Induced Macrocycle and Coordination Polymer Formation upon Combination of 2,5-Pyridinedicarboxylate with Diorganotin Moieties

Vasquez‐Ríos

Rojas-León

Montes-Tolentino

et al. 2018

Crystal Growth & Design

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Ligands derived from 2,x- and 3,y-pyridinedicarboxylic acid (x = 3–6; y = 4–5) are widely used building blocks for the formation of metal-coordination polymers (MCPs), as they show a large variety of bridging modes and angles. Metal complexation occurs either only with the carboxylate groups or through N,O-chelate ring formation. In this contribution, the supramolecular chemistry and solvatomorphism of diorganotin complexes with 2,5-pyridinedicarboxylate (25pdc) formed in the presence of a series of coordinating and noncoordinating solvents were explored in detail. Five novel diorganotin 25pdc’s of composition [Me2Sn(25pdc)(py)]3·3.04C5H5N·1.86H2O (1), {[Me2Sn(25pdc)]·[Me2Sn(25pdc)(H2O)]} n 2nC7H8O (2), {[nBu2Sn(25pdc)]4} n ·4nC6H5NO2 (3), [nBu2Sn(25pdc)(gly)] n (4), and {[nBu2Sn·(25pdc)]3} n ·nCHCl3 (5) were achieved and analyzed in the context of previously reported tri- and diorganotin complexes with the same ligand. The comparative study revealed that upon coordination to diorganotin species the ligand exhibits N,O-chelate ring formation with the carboxylate group in the 2-position and bridging to other tin atoms primarily by the 5-carboxylate group, giving macrocyclic, one-, two-, or three-dimensional MCPs. On the contrary, triorganotin moieties are mostly bound only by the ligand carboxylate groups without N→Sn binding. The assemblies of diorganotin 25pdc’s mostly contain trinuclear or tetranuclear macrocycles with a large predominance of the generally uncommon [3 + 3] metal–organic aggregates. For the trinuclear macrocycles, different configurations having 12-, 18-, 21-, or 27-membered rings were encountered. The metal atoms in diorganotin 25pdc’s prefer pentagonal-bipyramidal environments, which are achieved through coordination by solvent molecules (H2O, DMSO, py) or intermolecular O→Sn bond formation. In solution, di-n-butyltin 25pdc exhibits supramolecular isomerism, giving a tetrameric aggregate in the noncoordinating solvent chloroform and a trimeric species in the presence of coordinating solvents, such as DMSO, pyridine, or methanol, due to solvent→Sn bond formation.

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“…Research into organotin(IV) carboxylates continues to be plentiful, as the different coordination numbers and geometries about the tin provide a number of structural possibilities (Tiekink , 1994 ;Garcia -Zarracino and Hoepfl , 2005a ;Deak and Tarkanyi , 2006 ). To date, there are no known difuctional tin-carboxylate BINOL precursors synthesized using organotin(IV) carboxylates.…”

Section: Introductionmentioning

confidence: 99%

Chiral rings from BINOL dicarboxylic acids and alkane ditin(IV) linkers

Seter

Dakternieks

Duthie³

2012

Main Group Metal Chemistry

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The fi rst series of building blocks for metal-organic frameworks (MOFs) utilizing the ( S )-2,2 ′ -diethoxy-1,1 ′ -binaphthyl-6,6 ′ -dicarboxylic acid ligand linked with a number of α , ω -bis(chlorodiorganostannyl) alkane spacers and α , ω -bis(dichloroorganostannyl) alkane spacers has been synthesized and characterized. The new compounds have been shown to form monomeric chiral rings with the potential to generate large coordination networks. The potential formation of chiral supramolecular and polymeric materials from the chiral precursors was explored by investigating the structures that form as a result of the hypervalency available at metal centers. These chiral compounds were built using the concept that stemmed from the construction of MOFs. The ' pre-organized ' chiral rings synthesized here can potentially fi nd use in chiral catalysis, enantioselective synthesis and in designing chiral polymers.

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Structural characterization of dimethyl‐ and di‐n‐butyltin(IV) 2,3‐pyridinedicarboxylate in solution and in the solid state

Cited by 12 publications

References 45 publications

Influence of Aromatic Substituents on the Supramolecular Architectures of Monoorganooxotin Drums

Influence of Aromatic Substituents on the Supramolecular Architectures of Monoorganooxotin Drums

Pyridinedicarboxylic Acids as Versatile Building Blocks for Coordination-Driven Self-Assembly: Solvent-Induced Macrocycle and Coordination Polymer Formation upon Combination of 2,5-Pyridinedicarboxylate with Diorganotin Moieties

Chiral rings from BINOL dicarboxylic acids and alkane ditin(IV) linkers

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